The invention relates to new 1-H-3-aryl-pyrrolidine-2,4-dione derivatives, to a plurality of processes for their preparation, and to their use as pesticides, in particular as insecticides and acaricides.
3-Acyl-pyrrolidine-2,4-diones have previously been described as having pharmaceutical properties (S. Suzuki et al. Chem. Pharm. Bull. 15 1120 (1967)). Moreover, N-phenylpyrrolidine-2,4-diones have been synthesized by R. Schmierer and H. Mildenberger (Liebigs Ann. Chem. 1985 1095). A biological activity of these compounds has not been described.
EP-A 0 262 399 and GB-A 2 266 888 disclose compounds of a similar structure (3-aryl-pyrrolidine-2,4-diones), but nothing has been disclosed about them having a herbicidal, insecticidal or acaricidal activity. Known, and having a herbicidal, insecticidal or acaricidal activity, are unsubstituted bicyclic 3-aryl-pyrrolidine-2,4-dione derivatives (EP-A 355 599 and EP 415 211) and substituted monocyclic 3-aryl-pyrrolidine-2,4-dione derivatives (EP-A 377 893 and EP 442 077).
Substances which are furthermore known are polycyclic 3-aryl-pyrrolidine-2,4-dione derivatives (EP 442 073) and 1-H-3-aryl-pyrrolidine-dione derivatives (EP 456 063 and EP 521 334).
New substituted 1-H-3-aryl-pyrrolidine-2,4-dione derivatives have now been found, of the formula (I) 
in which
A represents hydrogen, or represents alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl or alkylthioalkyl, in each case optionally substituted by halogen, or represents cycloalkyl which is optionally interrupted by at least one hetero atom, or represents aryl, arylalkyl or hetaryl, in each case optionally substituted by halogen, alkyl, halogenoalkyl, alkoxy or nitro,
B represents hydrogen, alkyl or alkoxyalkyl, or
A and B together with the carbon atom to which they are bonded represent a saturated or unsaturated, unsubstituted or substituted cycle which is optionally interrupted by at least one hetero atom,
X represents halogen or alkoxy,
Y represents hydrogen, halogen or alkoxy,
Z represents hydrogen, halogen or alkoxy,
G represents hydrogen (a) or the groups 
E represents a metal ion equivalent or an ammonium ion,
L and M in each case represent oxygen or sulfur,
R1 represents alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl or cycloalkyl which can be interrupted by hetero atoms, in each case optionally substituted by halogen, or represents optionally substituted phenyl or in each case optionally substituted phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl,
R2 represents alkyl, alkenyl, alkoxyalkyl or polyalkoxyalkyl, in each case optionally substituted by halogen, or represents in each case optionally substituted cycloalkyl, phenyl or benzyl,
R3, R4 and R5 independently of one another represent alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio or cycloalkylthio, in each case optionally substituted by halogen, or represent in each case optionally substituted phenyl, phenoxy or phenylthio,
R6 and R7 independently of one another represent hydrogen, or represent alkyl, cycloalkyl, alkenyl, alkoxy or alkoxyalkyl, in each case optionally substituted by halogen, or represent optionally substituted phenyl, or represent optionally substituted benzyl, or together with the N atom to which they are bonded represent a cycle which is optionally interrupted by oxygen or sulfur, with the proviso that X and Y or X and Z do not simultaneously represent halogen.
Taking into account the various meanings (a), (b), (c), (d), (e) (f) and (g) of group G of the general formula (I), the following main structures (Ia) to (Ig) result: 
in which
A, B, E, L, M, X, Y, Z, R1, R2, R3, R4, R5, R6 and R7 have the abovementioned meanings.
Because of one or more chiral centers, the compounds of the formulae (Ia)-(Ig) are generally obtained in the form of a mixture of stereoisomers which, if appropriate, can be separated in the customary manner. They can be used in the form of their diastereomer mixtures as well as in the form of the pure diastereomers or enantiomers. For simplicity""s sake, the following text will always mention compounds of the formulae (Ia) to (Ig), even though this is to be understood as meaning the pure compounds as well as the mixtures comprising various proportions of isomeric, enantiomeric and stereomeric compounds.
Furthermore, it has been found that the new substituted 1-H-3-aryl-pyrrolidine-2,4-dione derivatives of the formula (I) are obtained by one of the processes described below:
(A) 1-H-3-aryl-pyrrolidine-2,4-diones or their enols of the formula (Ia) 
xe2x80x83in which
A, B, X, Y and Z have the abovementioned meanings, are obtained when
xcex1) N-acylamino acid esters of the formula (II) 
xe2x80x83in which
A, B, X, Y and Z have the abovementioned meanings, and
R8 represents alkyl are subjected to an intramolecular condensation reaction in the presence of a diluent and in the presence of a base; or
xcex2) 1-H-3-aryl-pyrrolidine-2,4-diones or their enols of the formula (Ia-a) 
xe2x80x83in which
A, B, X and Z have the abovementioned meanings, and
Y1 represents xe2x80x94OR8, where
R8 represents alkyl, are obtained when N-acylamino acid esters of the formula (IIa) 
xe2x80x83in which
A, B, X and Z have the abovementioned meanings,
Y2 represents fluorine and
R8 represents alkyl, preferably C1-C8-alkyl, are subjected to an intramolecular condensation reaction in the presence of a diluent and in the presence of a base; or
(B) compounds of the formula (Ib) 
xe2x80x83in which
A, B, X, Y, Z and R1 have the abovementioned meanings, are obtained when compounds of the formula (Ia), 
xe2x80x83in which
A, B, X, Y and Z have the abovementioned meanings, are reacted
xcex1) with acid halides of the general formula (III) 
xe2x80x83in which
R1 has the abovementioned meaning and
Hal represents halogen, in particular chlorine or bromine, if appropriate in the presence of a diluent and if appropriate in the presence of an acid-binding agent, or
xcex2) with carboxylic anhydrides of the general formula (IV)
R1xe2x80x94COxe2x80x94Oxe2x80x94COxe2x80x94R1xe2x80x83xe2x80x83(IV)
xe2x80x83in which
R1 has the abovementioned meaning, if appropriate in the presence of a diluent and if appropriate in the presence of an acid-binding agent; or
(C) compounds of the formula (Ic-a) 
xe2x80x83in which
A, B, X, Y, Z and R2 have the abovementioned meanings, and
M represents oxygen or sulfur are obtained when compounds of the formula (Ia) 
xe2x80x83in which
A, B, X, Y and Z have the abovementioned meanings, are reacted with chloroformic esters or chloroformic thioesters of the general formula (V)
R2xe2x80x94Mxe2x80x94COxe2x80x94Clxe2x80x83xe2x80x83(V)
xe2x80x83in which
R2 and M have the abovementioned meanings, if appropriate in the presence of a diluent and if appropriate in the presence of an acid-binding agent; or
(D) compounds of the formula (Ic-b) 
xe2x80x83in which
A, B, R2, X, Y and Z have the abovementioned meanings and
M represents oxygen or sulfur are obtained when compounds of the formula (Ia) 
xe2x80x83in which
A, B, X, Y and Z have the abovementioned meanings are reacted
xcex1) with chloromonothioformic esters or chlorodithioformic esters of the general formula (VI) 
xe2x80x83in which
M and R2 have the abovementioned meanings, if appropriate in the presence of a diluent and if appropriate in the presence of an acid-binding agent, or
xcex2) with carbon disulfide and then with alkyl halides of the general formula (VII)
R2xe2x80x94Halxe2x80x83xe2x80x83(VII)
xe2x80x83in which
R2 has the abovementioned meaning and
Hal represents chlorine, bromine or iodine; or
(E) compounds of the formula (Id) 
xe2x80x83in which
A, B, X, Y, Z and R3 have the abovementioned meanings are obtained when compounds of the formula (Ia) 
xe2x80x83in which
A, B, X, Y and Z have the abovementioned meanings are reacted with sulfonyl chlorides of the general formula (VIII)
R3xe2x80x94SO2xe2x80x94Clxe2x80x83xe2x80x83(VIII)
xe2x80x83in which
R3 has the abovementioned meaning, if appropriate in the presence of a diluent and if appropriate in the presence of an acid-binding agent, or
(F) 1-H-3-aryl-pyrrolidine-2,4-diones of the formula (Ie) 
xe2x80x83in which
A, B, L, X, Y, Z, R4 and R5 have the abovementioned meanings are obtained when
1-H-3-aryl-pyrrolidine-2,4-diones of the formula (Ia) or their enols 
xe2x80x83in which
A, B, X, Y and Z have the abovementioned meanings are reacted with phosphorus compounds of the general formula (IX) 
xe2x80x83in which
L, R4 and R5 have the abovementioned meanings and
Hal represents halogen, in particular chlorine or bromine; or
(G) compounds of the formula (If) 
xe2x80x83in which
A, B, X, Y ana Z have the abovementioned meanings and
E represents a metal ion equivalent or an ammonium ion are obtained when compounds of the formula (Ia) 
xe2x80x83in which
A, B, X, Y and Z have the abovementioned meanings are reacted with metal compounds or amines of the general formulae (X) and (XI)
Me(OR9)txe2x80x83xe2x80x83(X)

xe2x80x83in which
Me represents mono- or divalent metal ions,
t represents the number 1 or 2 and
R9, R10 and R11 independently of one another represent hydrogen and/or alkyl, if appropriate in the presence of a diluent.
(H) Furthermore, it has been found that compounds of the formula (Ig) 
xe2x80x83in which
A, B, L, X, Y, X, R6 and R7 have the abovementioned meanings are obtained when compounds of the formula (Ia) 
xe2x80x83in which
A, B, X, Y and Z have the abovementioned meanings are reacted
xcex1) with isocyanates or isothiocyanates of the general formula (XII)
R6xe2x80x94Nxe2x95x90Cxe2x95x90Lxe2x80x83xe2x80x83(XII)
xe2x80x83in which
R6 has the abovementioned meaning, if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst, or
xcex2) with carbamoyl chlorides or thiocarbamoyl chlorides of the general formula (XIII) 
xe2x80x83in which
L, R6 and R7 have the abovementioned meanings, if appropriate in the presence of a diluent and if appropriate in the presence of an acid-binding agent.
Furthermore, it has been found that the new 1-H-3-aryl-pyrrolidine-2,4-dione derivatives of the formula (I) are distinguished by outstanding insecticidal and acaricidal activities. Furthermore, compounds of the formula (I) have herbicidal and fungicidal secondary effects.
The following applies to the general formulae of the present application:
A preferably represents hydrogen, or represents C1-C12-alkyl, C3-C8-alkenyl, C1-C10-alkoxy-C2-C8-alkyl, C1-C8-polyalkoxy-C2-C8-alkyl, C1-C10-alkylthio-C2-C6-alkyl or cycloalkyl having 3 to 8 ring atoms which can optionally be interrupted by oxygen and/or sulfur, in each case optionally substituted by halogen, or represents aryl, hetaryl or aryl-C1-C6-alkyl, in each case optionally substituted by halogen, C1-C6-alkyl, C1-C6-halogenoalkyl, C1-C6-alkoxy, and/or nitro.
B preferably represents hydrogen, or represents C1-C12-alkyl or C1-C8-alkoxyalkyl, or
A, B and the carbon atom to which they are bonded preferably represent a saturated or unsaturated C3-C10-spirocycle which is optionally monosubstituted or polysubstituted by alkyl, cycloalkyl, halogenoalkyl, alkoxy, thioalkyl, halogen or phenyl and optionally interrupted by oxygen or sulfur, or
A, B and the carbon atom to which they are bonded preferably represent a C3-C6-spirocycle which is substituted by an alkylenediyl group which is optionally interrupted by one or two oxygen and/or sulfur atoms or substituted by an alkylenedioxy or by an alkylenedithioyl group and this alkylenediyl, alkylenedioxy or alkylenedithioyl group together with the carbon atom to which it is bonded forms a further five- to eight-membered spirocycle, or
A, B and the carbon atom to which they are bonded preferably represent a C3-C8-spirocycle in which two substituents together represent a saturated or unsaturated five- or six-membered cycle which is optionally substituted by alkyl, alkoxy or halogen and which can be interrupted by oxygen or sulfur.
A particularly preferably represents hydrogen, or represents C1-C10-alkyl, C3-C6-alkenyl, C1-C8-alkoxy-C2-C6-alkyl, C1-C6-polyalkoxy-C2-C6-alkyl, C1-C8-alkylthio-C2-C6-alkyl or cycloalkyl having 3 to 7 ring atoms which can be interrupted by 1 to 2 oxygen and/or sulfur atoms, in each case optionally substituted by halogen, or represents phenyl, thienyl, pyridyl, imidazolyl, pyrazolyl, triazolyl, indolyl, thiazolyl or phenyl-C1-C4-alkyl, in each case optionally substituted by halogen, C1-C4-alkyl, C1-C4-halogenoalkyl, C1-C4-alkoxy and/or nitro.
B particularly preferably represents hydrogen, C1-C10-alkyl or C1-C6-alkoxyalkyl, or
A, B and the carbon atom to which they are bonded particularly preferably represent a saturated or unsaturated C3-C9-spirocycle which is optionally monosubstituted or polysubstituted by C1-C6-alkyl, C3-C8-cycloalkyl, C1-C3-halogenoalkyl, C1-C6-alkoxy, C1-C6-thioalkyl, fluorine, chlorine or phenyl and which is optionally interrupted by oxygen or sulfur, or
A, B and the carbon atom to which they are bonded particularly preferably represent a C3-C6-spirocycle which is substituted by an alkylenediyl group which is optionally interrupted by one or two oxygen or sulfur atoms or substituted by an alkylenedioxy or by an alkylenedithiol group, and this alkylenediyl, alkylenedioxy or alkylenedithiol group together with the carbon atom to which it is bonded forms a further five- to seven-membered spirocycle, or
A, B and the carbon atom to which they are bonded particularly preferably represent a C3-C6-spirocycle in which two adjacent substituents together represent a saturated or unsaturated five- or six-membered cycle which is substituted by C1-C3-alkyl, C1-C3-alkoxy, fluorine, chlorine or bromine and which can be interrupted by oxygen or sulfur.
A very particularly preferably represents hydrogen, or represents C1-C8-alkyl, C3-C4-alkenyl, C1-C6-alkoxy-C2-C4-alkyl, C1-C4-polyalkoxy-C2-C4-alkyl, C1-C6-alkylthio-C2-C4-alkyl or cycloalkyl having 3 to 6 ring atoms which can be interrupted by 1 to 2 oxygen and/or sulfur atoms, in each case optionally substituted by halogen, or represents phenyl, thienyl, pyridyl, imidazolyl, pyrazolyl, triazolyl, indolyl, thiazolyl or phenyl-C1-C3-alkyl, in each case optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, propyl, iso-propyl, methoxy, ethoxy, trifluoromethyl and/or nitro.
B very particularly preferably represents hydrogen, C1-C8-alkyl or C1-C4-alkoxyalkyl, or
A, B and the carbon atom to which they are bonded very particularly preferably represent a saturated or unsaturated C3-C8-spirocycle which is optionally monosubstituted or polysubstituted by methyl, ethyl, propyl, isopropyl, butyl, iso-butyl, sec-butyl, tert-butyl, cyclohexyl, trifluoromethyl, methoxy, ethoxy, propoxy, iso-propoxy, butoxy, iso-butoxy, sec-butoxy, tert-butoxy, methylthio, ethylthio, fluorine, chlorine or phenyl and optionally interrupted by oxygen or sulfur, or
A, B and the carbon atom to which they are bonded v particularly preferably represent a C3-C6-spirocycle which is substituted by an alkylenediyl group which is optionally interrupted by an oxygen or sulfur atom or by an alkylenedioxy group, and this alkylenediyl or alkylenedioxy group together with the carbon atom to which it is bonded forms a further five- to seven-membered spirocycle, or
A, B and the carbon atom to which they are bonded very particularly preferably represent a C3-C6-spirocycle in which two substituents together represent a saturated or unsaturated five- or six-membered cycle which can be interrupted by oxygen or sulfur.
X preferably represents halogen or C1-C6-alkoxy.
X particularly preferably represents halogen or C1-C4-alkoxy.
X very particularly preferably represents fluorine, chlorine, bromine, methoxy, ethoxy, propoxy or iso-propoxy.
Y preferably represents hydrogen, halogen or C1-C6-alkoxy.
Y particularly preferably represents hydrogen, halogen or C1-C4-alkoxy.
Y very particularly preferably represents hydrogen, fluorine, chlorine, bromine, methoxy, ethoxy, propoxy or iso-propoxy.
Z preferably represents hydrogen, halogen or C1-C6-alkoxy.
Z particularly preferably represents hydrogen, halogen or C1-C4-alkoxy.
Z very particularly preferably represents hydrogen, fluorine, chlorine, bromine, methoxy, ethoxy, propoxy or iso-propoxy.
In each case, X and Y or X and Z do not simultaneously represent halogen.
G preferably represents hydrogen (a) or the groups 
xe2x80x83in which
E represents a metal ion equivalent or an ammonium ion and
L and M in each case represent oxygen or sulfur.
R1 preferably represents C1-C20-alkyl, C2-C20-alkenyl, C1-C8-alkoxy-C1-C8-alkyl, C1-C8-alkylthio-C1-C8-alkyl, C1-C8-polyalkoxy-C2-C8-alkyl or cycloalkyl having 3 to 8 ring atoms which can be interrupted by oxygen and/or sulfur atoms, in each case optionally substituted by halogen,
phenyl which is optionally substituted by halogen, nitro, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-halogenoalkyl, C1-C6-halogenoalkoxy, C1-C6-alkylthio or C1-C6-alkyl-sulfonyl,
phenyl-C1-C6-alkyl which is optionally substituted by halogen, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-halogenoalkyl or C1-C6-halogenoalkoxy,
hetaryl which is optionally substituted by halogen and/or C1-C6-alkyl,
phenoxy-C1-C6-alkyl which is optionally substituted by halogen and/or C1-C6-alkyl,
hetaryloxy-C1-C5-alkyl which is optionally substituted by halogen, amino and/or C1-C6-alkyl.
R2 preferably represents C1-C20-alkyl, C3-C20-alkenyl, C1-C8-alkoxy-C2-C8-alkyl or C1-C8-polyalkoxy-C2-C8-alkyl, in each case optionally substituted by halogen,
C3-C8-cycloalkyl which is optionally substituted by halogen, C1-C4-alkyl and/or C1-C4-alkoxy, or
phenyl or benzyl, in each case optionally substituted by halogen, nitro, C3-C6-alkyl, C1-C4-alkoxy and/or C1-C6-halogenoalkyl,
R3, R4 and R5 independently of one another preferably represent C1-C8-alkyl, C1-C8-alkoxy, C1-C8-alkylamino, di-(C1-C8)-alkylamino, C1-C8-alkylthio, C3-C6-alkenylthio or C3-C7-cycloalkylthio, in each case optionally substituted by halogen, or represent phenyl, phenoxy or phenylthio, in each case optionally substituted by halogen, nitro, cyano, C1-C4-alkoxy, C1-C4-halogenoalkoxy, C1-C4-alkylthio, C1-C4-halogenoalkylthio, C1-C4-alkyl or C1-C4-halogenoalkyl,
R6 and R7 independently of one another preferably represent hydrogen, C1-C8-alkyl, C3-C8-cycloalkyl, C1-C8-alkoxy, C3-C8-alkenyl or C1-C8-alkoxy-C2-C8-alkyl, in each case optionally substituted by halogen, or represent phenyl which is optionally substituted by halogen, C1-C8-halogenoalkyl, C1-C8-alkyl and/or C1-C8-alkoxy, or represent benzyl which is optionally substituted by halogen, C1-C8-alkyl, C1-C8-halogenoalkyl and/or C1-C8-alkoxy, or together with the N atom to which they are bonded represent a C3xe2x80x94C6-alkylene ring which is optionally interrupted by oxygen or sulfur.
G particularly preferably represents hydrogen (a) or the groups 
xe2x80x83in which
E represents a metal ion equivalent or an ammonium ion,
L and M in each case represent oxygen or sulfur,
R1 particularly preferably represents C1-C16-alkyl, C2-C16-alkenyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkyl-thio-C1-C6-alkyl, C1-C6-polyalkoxy-C2-C6-alkyl or cycloalkyl having 3 to 7 ring atoms which can be interrupted by 1 or 2 oxygen and/or sulfur atoms, in each case optionally substituted by halogen,
phenyl which is optionally substituted by halogen, nitro, C1-C4-alkyl, C1-C4-alkoxy, C1-C3-halogenoalkyl, C1-C3-halogenoalkoxy, C1-C4-alkylthio and/or C1-C4-alkylsulfonyl,
phenyl-C1-C4-alkyl which is optionally substituted by halogen, C1-C4-alkyl, C1-C4-alkoxy, C1-C3-halogenoalkyl or C1-C3-halogenoalkoxy,
thienyl, furanyl, pyridyl, pyrimidyl, thiazolyl or pyrazolyl, in each case optionally substituted by fluorine, chlorine, bromine and/or C1-C4-alkyl,
phenoxy-C1-C5-alkyl which is optionally substituted by fluorine, chlorine, bromine and/or C1-C4-alkyl, or
pyridyloxy-C1-C5-alkyl, pyrimidyloxy-C1-C5-alkyl or thiazolyloxy-C1-C5-alkyl, in each case optionally substituted by fluorine, chlorine, bromine, amino and/or C1-C4-alkyl.
R2 particularly preferably represents C1-C16-alkyl, C3-C16-alkenyl, C1-C6-alkoxy-C2-C6-alkyl or C1-C6-polyalkoxy-C2-C6-alkyl, in each case optionally substituted by halogen,
C3-C7-cycloalkyl which is optionally substituted by halogen, C1-C3-alkyl and/or C1-C3-alkoxy, or
phenyl or benzyl, in -each case optionally substituted by halogen, nitro, C1-C4-alkyl, C1-C3-alkoxy and/or C1-C3-halogenoalkyl.
R3, R4 and R5 independently of one another particularly preferably represent C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylamino, Di-(C1-C6)-alkylamino, C1-C6-alkylthio, C3-C4-alkenylthio or C3-C6-cycloalkylthio, in each case optionally substituted by halogen, or phenyl, phenoxy or phenylthio, in each case optionally substituted by fluorine, chlorine, bromine, nitro, cyano, C1-C3-alkoxy, C1-C3-halogenoalkoxy, C1-C3-alkylthio, C1-C3-halogenoalkylthio, C1-C3-alkyl or C1-C3-halogenoalkyl.
R6 and R7 independently of one another particularly preferably represent hydrogen, or C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C3-C6-alkenyl or C1-C6-alkoxy-C2-C6-alkyl, in each case optionally substituted by halogen, or phenyl which is optionally substituted by halogen, C1-C5-halogenoalkyl, C1-C5-alkyl and/or C1-C5-alkoxy, or benzyl which is optionally substituted by halogen, C1-C5-alkyl, C1-C5-halogenoalkyl, and/or C1-C5-alkoxy, or together with the N atom to which they are bonded a C3-C6-alkylene ring which is optionally interrupted by oxygen or sulfur.
G very particularly preferably represents hydrogen (a) or the groups 
xe2x80x83in which
E represents a metal ion equivalent or an ammonium ion and
L and M in each case represent oxygen or sulfur.
R1 very particularly preferably represents C1-C14-alkyl, C2-C14-alkenyl, C1-C4-alkoxy-C1-C6-alkyl, C1-C4-alkyl-thio-C1-C6-alkyl, C1-C4-polyalkoxy-C2-C4-alkyl or cycloalkyl having 3 to 6 ring atoms which can be interrupted by 1 to 2 oxygen, and/or sulfur atoms, in each case optionally substituted by fluorine and/or chlorine,
phenyl which is optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, propyl, i-propyl, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy, methylthio, ethylthio, methylsulfonyl, ethylsulfonyl and/or nitro,
phenyl-C1-C3-alkyl which is optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, propyl, i-propyl, methoxy, ethoxy, trifluoromethyl and/or trifluoromethoxy,
thienyl, furanyl, pyridyl, pyrimidyl, thiazolyl or pyrazolyl, in each case optionally substituted by fluorine, chlorine, bromine, methyl and/or ethyl,
phenoxy-C1-C4-alkyl which is optionally substituted by fluorine, chlorine, methyl and/or ethyl, or
pyridyloxy-C1-C4-alkyl, pyrimidyloxy-C1-C4-alkyl or thiazolyloxy-C1-C4-alkyl, in each case optionally substituted by fluorine, chlorine, amino, methyl and/or ethyl.
R2 very particularly preferably represents C1-C14-alkyl, C3-C14-alkenyl, C1-C4-alkoxy-C2-C6-alkyl or C1-C4-polyalkoxy-C2-C6-alkyl, in each case optionally substituted by fluorine and/or chlorine,
C3-C6-cycloalkyl which is optionally substituted by fluorine, chlorine, methyl, ethyl, propyl, iso-propyl and/or methoxy,
or phenyl or benzyl, in each case optionally substituted by fluorine, chlorine, nitro, methyl, ethyl propyl, i-propyl, methoxy, ethoxy and/or trifluoromethyl.
R3, R4 and R5 very particularly preferably independently of one another represent C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylamino, di-(C1-C4) -alkylamino or C1-C4-alkylthio, in each case optionally substituted by fluorine and/or chlorine, or phenyl, phenoxy or phenylthio, in each case optionally substituted by fluorine, chlorine, bromine, nitro, cyano, C1-C2-alkoxy, C1-C2-fluoroalkoxy, C1-C2-alkylthio, C1-C2-fluoroalkylthio and/or C1-C3-alkyl.
R6 and R7 very particularly preferably independently of one another represent hydrogen, or C1-C4-alkyl, C3-C6-cycloalkyl, C1-C4-alkoxy, C3-C4-alkenyl or C1-C4-alkoxy-C2-C4-alkyl, in each case optionally substituted by fluorine, chlorine and/or bromine, or phenyl which is optionally substituted by fluorine, chlorine, bromine, C1-C4-halogenoalkyl, C1-C4-alkyl and/or C1-C4-alkoxy, or benzyl which is optionally substituted by fluorine, chlorine, bromine, C1-C4-alkyl, C1-C4-halogenoalkyl, and/or C1-C4-alkoxy, or together with the N atom to which they are bonded a C3-C6-alkylene ring which is optionally interrupted by oxygen or sulfur.
Unless otherwise specified, alkyl radicals, also in connection with hetero atoms such as, for example, in alkoxy, are in each case straight-chain or branched as far as this is possible.
The general definitions of radicals or illustrations, or the preferred ranges of the definitions of radicals or illustrations, which have been mentioned above can be combined with each other as desired, that is to say that combinations between the specific ranges and preferred ranges are also possible. They apply to the end product and, analogously, to the precursors and intermediates.
Preferred according to the invention are those compounds of the general formula (I) which show a combination of the meanings given above as being preferred (which are preferable).
Particularly preferred according to the invention are those compounds of the general formula (I) which show a combination of the meanings given above as being particularly preferred.
Very particularly preferred according to the invention are those compounds of the general formula (I) which show a combination of the meanings given above as being very particularly preferred.
The following compounds of the formula (Ia) may be mentioned individually in addition to the compounds mentioned in the preparation examples:
The following compounds of the formula (Ib) may be mentioned individually in addition to the compounds mentioned in the preparation examples:
The following compounds of the formula (Ic) may be mentioned individually in addition to the compounds mentioned in the preparation examples:
The following compounds of the formula (Id) may be mentioned individually in addition to the compounds mentioned in the preparation examples:
The following compounds of the formula (Ie) may be mentioned individually in addition to the compounds mentioned in the preparation examples:
The following compounds of the formula (If-a) may be mentioned individually in addition to the compounds mentioned in the preparation examples:
The following compounds of the formula (If-b) may be mentioned individually in addition to the compounds mentioned in the preparation examples:
The following compounds of the formula (Ig-a) may be mentioned individually in addition to the compounds mentioned in the preparation examples:
The following compounds of the formula (Ig-b) may be mentioned individually in addition to the compounds mentioned in the preparation examples:
If, in accordance with process (Axcex1), ethyl N-(2-chloro-4-methoxyphenylacetyl)-1-amino-4-ethyl-cyclohexane-carboxylate is used as starting substance, the course of the process according to the invention can be represented by the following equation: 
If, in accordance with process (Axcex2), methyl N-(2-chloro-4-fluorophenylacetyl)-2-amino-2,3-dimethyl-butyrate is used as starting substance, the course of the process according to the invention can be represented by the following equation: 
If, in accordance with process (Bxcex1), 3-(2-chloro-6-methoxyphenyl-5,5-dimethyl-pyrrolidine-2,4-dione and pivaloyl chloride are used as starting substances, the course of the process according to the invention can be represented by the following equation: 
If, in accordance with process (Bxcex2), 3-(2-bromo-6-methoxyphenyl)-5-isopropyl-5-methyl-pyrrolidine-2,4-dione and acetic anhydride are used as starting compounds, the course of the process according to the invention can be represented by the following equation: 
If, in accordance with process (C), 3-(2-methoxy-2-chlorophenyl)-5,5-diethyl-pyrrolidine-2,4-dione and ethoxyethyl chloroformate are used as starting compounds, the course of the process according to the invention can be represented by the following equation: 
If, in accordance with process (Dxcex1), 3-(2-chloro-4-methoxyphenyl)-5,5-pentamethylene-pyrrolidine-2,4-dione and methyl chloromonothioformate are used as starting materials, the course of the reaction can be represented as follows: 
If, in accordance with process (Dxcex2), 3-(2-bromo-4-ethoxy-phenyl)-5,5-ethylmercaptoethyl-pyrrolidine-2,4-dione, carbon disulfide and methyl iodide are used as starting components, the course of the reaction can be represented as follows: 
If, in accordance with process (E), 3-(2-chloro-4-isopropoxy-phenyl)-5,5-(2-methyl)-pentamethylene-pyrrolidine-2,4-dione and methanesulfonyl chloride are used as starting materials, the course of the reaction can be represented by the following equation: 
If, in accordance with process (F), 3-(2-methoxy-4-chlorophenyl)-5-isobutyl-5-methyl-pyrrolidine-2,4-dione and 2,2,2-trifluoroethyl methanechlorothiophosphate are used as starting materials, the course of the reaction can be represented by the following equation: 
If, in accordance with process (G), 3-(2,4-dimethoxy-phenyl)-5-cyclopropyl-5-methyl-pyrrolidine-2,4-dione and NaOH are used as components, the course of the process according to the invention can be represented by the following equation: 
If, in accordance with process (Hxcex1), 3-(2-chloro-4-ethoxyphenyl)-5,5-hexamethylene-pyrrolidine-2,4-dione and ethyl isocyanate are used as starting materials, the course of the reaction can be represented by the following equation: 
If, in accordance with process (Hxcex2), 3-(2-methoxy-4-chlorophenyl)-5-methyl-pyrrolidine-2,4-dione and dimethylcarbamoyl chloride are used as starting materials, the course of the reaction can be represented by the following equation: 
The compounds of the formula (II) 
in which
A, B, X, Y, Z and R2 have the abovementioned meanings, which are required as starting substances in processes (A) according to the invention, are new.
Acyl-amino acid esters of the formula (II) are obtained, for example, when amino acid derivatives of the formula (XIV) 
in which
R12 represents hydrogen (XIVa) or alkyl (XIVb) and
A and B have the abovementioned meanings are acylated with phenylacetyl halides of the formula (XV) 
xe2x80x83in which
X, Y and Z have the abovementioned meanings and
Hal represents chlorine or bromine,
(Chem. Reviews 52, 237-416 (1953); Bhattacharya, Indian J. Chem. 6, 341-5, 1968) and, if R12xe2x80x2=hydrogen, the resulting acylamine acids of the formula (IIa) 
in which
A, B, X, Y and Z have the abovementioned meanings are esterified (Chem. Ind. (London) 1568 (1968)).
The substituted cyclic aminocarboxylic acids of the formula (XIVa) are generally obtainable by a Bucherer-Bergs reaction or by Strecker synthesis and are obtained in each case in various isomeric forms. Under the conditions of a Bucherer-Bergs reaction, for example, the result of predominantly those isomers (for simplicity""s sake term xcex2 hereinafter) in which the radicals R and the carboxyl group are in the equatorial position, while the conditions of Strecker synthesis give predominantly those isomers (for simplicity""s sake termed xcex1 hereinafter) in which the amino group and the radicals R are in the equatorial position. 
(L. Munday,. J. Chem. Soc. 4372 (1961); J. T. Eward, C. Jitrangeri, Can. J. Chem. 53, 3339 (1975).
Moreover, the starting substances of the formula (II) 
in which
A, B, X, Y, Z and R8 have the abovementioned meanings, which are used in the above processes (A) can be prepared when aminonitriles of the formula (XVI) 
xe2x80x83in which
A and B have the abovementioned meanings are reacted with phenylacetyl halides of the formula (XV) 
in which
X, Y and Z have the abovementioned meanings and
Hal represents chlorine or bromine to give compounds of the formula (XVII) 
xe2x80x83in which
A, B, X, Y and Z have the abovementioned meanings, and these compounds are subsequently subjected to alcoholysis in the presence of sulfuric acid.
The compounds of the formula (XVII) are also new.
In addition to the intermediates mentioned in the preparation examples, the following compounds of the formula (II) may be mentioned by way of example, but not by way of limitation:
N-(2-chloro-4-methoxyphenylacetyl)-alanine methyl ester
N-(2-chloro-4-methoxyphenylacetyl)-leucine methyl ester
N-(2-chloro-4-methoxyphenylacetyl)-isoleucine methyl ester
N-(2-chloro-4-methoxyphenylacetyl)-valine methyl ester
methyl N-(2-chloro-4-methoxyphenylacetyl)-aminoisobutyrate
methyl N-(2-chloro-4-methoxyphenylacetyl)-2-ethyl-2-aminobutyrate
methyl N-(2-chloro-4-methoxyphenylacetyl)-2-methyl-2-aminovalerate
methyl N-(2-chloro-4-methoxyphenylacetyl)-2,3-dimethyl-2-aminovalerate
methyl N-(2-chloro-4-methoxyphenylacetyl)-1-amino-cyclopentanecarboxylate
methyl N-(2-chloro-4-methoxyphenylacetyl)-1-amino-cyclohexanecarboxylate
methyl N-(2-chloro-4-methoxyphenylacetyl)-1-amino-cycloheptanecarboxylate
methyl N-(2-chloro-4-methoxyphenylacetyl)-1-amino-cyclooctanecarboxylate
N-(4-chloro-2-methoxyphenylacetyl)-alanine methyl ester
N-(4-chloro-2-methoxyphenylacetyl)-leucine methyl ester
N-(4-chloro-2-methoxyphenylacetyl)-isoleucine methyl ester
N-(4-chloro-2-methoxyphenylacetyl)-valine methyl ester
methyl N-(4-chloro-2-methoxyphenylacetyl)-aminoisobutyrate
methyl N-(4-chloro-2-methoxyphenylacetyl)-2-ethyl-2-aminobutyrate
methyl N-(4-chloro-2-methoxyphenylacetyl)-2-methyl-2-aminovalerate
methyl N-(4-chloro-2-methoxyphenylacetyl)-2,3-dimethyl-2-aminovalerate
methyl N-(4-chloro-2-methoxyphenylacetyl)-1-amino-cyclopentanecarboxylate
methyl N-(4-chloro-2-methoxyphenylacetyl)-1-amino-cyclohexanecarboxylate
methyl N-(4-chloro-2-methoxyphenylacetyl)-1-amino-cycloheptanecarboxylate
methyl N-(4-chloro-2-methoxyphenylacetyl)-1-amino-cyclooctanecarboxylate
N-(2-chloro-6-methoxyphenylacetyl)-alanine methyl ester
N-(2-chloro-6-methoxyphenylacetyl)-leucine methyl ester
N-(2-chloro-6-methoxyphenylacetyl)-isoleucine methyl ester
N-(2-chloro-6-methoxyphenylacetyl)-valine methyl ester
methyl N-(2-chloro-6-methoxyphenylacetyl)-aminoisobutyrate
methyl N-(2-chloro-6-methoxyphenylacetyl)-2-ethyl-2-aminobutyrate
methyl N-(2-chloro-6-methoxyphenylacetyl)-2-methyl-2-aminovalerate
methyl N-(2-chloro-6-methoxyphenylacetyl)-2,3-dimethyl-2-aminovalerate
methyl N-(2-chloro-6-methoxyphenylacetyl)-1-amino-cyclopentanecarboxylate
methyl N-(2-chloro-6-methoxyphenylacetyl)-1-amino-cyclohexanecarboxylate
methyl N-(2-chloro-6-methoxyphenylacetyl)-1-amino-cycloheptanecarboxylate
methyl N-(2-chloro-6-methoxyphenylacetyl)-1-amino-cyclooctanecarboxylate
methyl N-(2-chloro-4-methoxy-phenylacetyl)-1-amino-2-methyl-cyclohexanecarboxylate
methyl N-(2-chloro-4-methoxy-phenylacetyl)-1-amino-3-methyl-cyclohexanecarboxylate
methyl N-(2-chloro-4-methoxy-phenylacetyl)-1-amino-4-methyl-cyclohexanecarboxylate
methyl N-(2-chloro-4-methoxy-phenylacetyl)-1-amino-3,4-dimethyl-cyclohexanecarboxylate
methyl N-(2-chloro-4-methoxy-phenylacetyl)-1-amino-4-ethyl-cyclohexanecarboxylate
methyl N-(2-chloro-4-methoxy-phenylacetyl)-1-amino-4-isopropyl-cyclohexanecarboxylate
methyl N-(2-chloro-4-methoxy-phenylacetyl)-1-amino-4-tert-butyl-cyclohexanecarboxylate
methyl N-(2-chloro-4-methoxy-phenylacetyl)-1-amino-4-methoxy-cyclohexanecarboxylate
methyl N-(2-chloro-6-methoxy-phenylacetyl)-1-amino-2-methyl-cyclohexanecarboxylate
methyl N-(2-chloro-6-methoxy-phenylacetyl)-1-amino-3-methyl-cyclohexanecarboxylate
methyl N-(2-chloro-6-methoxy-phenylacetyl)-1-amino-4-methyl-cyclohexanecarboxylate
methyl N-(2-chloro-6-methoxy-phenylacetyl)-1-amino-3,4-dimethyl-cyclohexanecarboxylate
methyl N-(2-chloro-6-methoxy-phenylacetyl)-1-amino-4-ethyl-cyclohexanecarboxylate
methyl N-(2-chloro-6-methoxy-phenylacetyl)-1-amino-4-isopropyl-cyclohexanecarboxylate
methyl N-(2-chloro-6-methoxy-phenylacetyl)-1-amino-4-tert-butyl-cyclohexanecarboxylate
methyl N-(2-chloro-6-methoxy-phenylacetyl)-1-amino-4-methoxy-cyclohexanecarboxylate
methyl N-(4-chloro-2-methoxy-phenylacetyl)-1-amino-2-methyl-cyclohexanecarboxylate
methyl N-(4-chloro-2-methoxy-phenylacetyl)-1-amino-3-methyl-cyclohexanecarboxylate
methyl N-(4-chloro-2-methoxy-phenylacetyl)-1-amino-4-methyl-cyclohexanecarboxylate
methyl N-(4-chloro-2-methoxy-phenylacetyl)-1-amino-3,4-dimethyl-cyclohexanecarboxylate
methyl N-(4-chloro-2-methoxy-phenylacetyl)-1-amino-4-ethyl-cyclohexanecarboxylate
methyl N-(4-chloro-2-methoxy-phenylacetyl)-1-amino-4-isopropyl-cyclohexanecarboxylate
methyl N-(4-chloro-2-methoxy-phenylacetyl)-1-amino-4-tert-butyl-cyclohexanecarboxylate
methyl N-(4-chloro-2-methoxy-phenylacetyl)-1-amino-4-methoxy-cyclohexanecarboxylate.
In addition to the intermediates mentioned in the preparation examples, the following compounds of the formula (IIa) may be mentioned by way of example, but not by way of limitation:
N-(2-chloro-4-methoxyphenylacetyl)-alanine
N-(2-chloro-4-methoxyphenylacetyl)-leucine
N-(2-chloro-4-methoxyphenylacetyl)-isoleucine
N-(2-chloro-4-methoxyphenylacetyl)-valine
N-(2-chloro-4-methoxyphenylacetyl)-aminoisobutyric acid
N-(2-chloro-4-methoxyphenylacetyl)-2-ethyl-2-aminobutyric acid
N-(2-chloro-4-methoxyphenylacetyl)-2-methyl-2-aminovaleric acid
N-(2-chloro-4-methoxyphenylacetyl)-2,3-dimethyl-2-aminovaleric acid
N-(2-chloro-4-methoxyphenylacetyl)-1-amino-cyclopentane-carboxylic acid
N-(2-chloro-4-methoxyphenylacetyl)-1-amino-cyclohexane-carboxylic acid
N-(2-chloro-4-methoxyphenylacetyl)-1-amino-cycloheptane-carboxylic acid
N-(2-chloro-4-methoxyphenylacetyl)-1-amino-cyclooctane-carboxylic acid
N-(4-chloro-2-methoxyphenylacetyl)-alanine
N-(4-chloro-2-methoxyphenylacetyl)-leucine
N-(4-chloro-2-methoxyphenylacetyl)-isoleucine
N-(4-chloro-2-methoxyphenylacetyl)-valine
N-(4-chloro-2-methoxyphenylacetyl)-aminoisobutyric acid
N-(4-chloro-2-methoxyphenylacetyl)-2-ethyl-2-2-aminobutyric acid
N-(4-chloro-2-methoxyphenylacetyl)-2-methyl-2-aminovaleric acid
N-(4-chloro-2-methoxyphenylacetyl)-2,3-dimethyl-2-aminovaleric acid
N-(4-chloro-2-methoxyphenylacetyl)-1-amino-cyclopentanecarboxylic acid
N-(4-chloro-2-methoxyphenylacetyl)-1-amino-cyclohexanecarboxylic acid
N-(4-chloro-2-methoxyphenylacetyl)-1-amino-cycloheptanecarboxylic acid
N-(4-chloro-2-methoxyphenylacetyl)-1-amino-cyclooctanecarboxylic acid
N-(2-chloro-6-methoxyphenylacetyl)-alanine
N-(2-chloro-6-methoxyphenylacetyl)-leucine
N-(2-chloro-6-methoxyphenylacetyl)-isoleucine
N-(2-chloro-6-methoxyphenylacetyl)-valine
N-(2-chloro-6-methoxyphenylacetyl)-aminoisobutyric acid
N-(2-chloro-6-methoxyphenylacetyl)-2-ethyl-2-aminobutyric acid
N-(2-chloro-6-methoxyphenylacetyl)-2-methyl-2-aminovaleric acid
N-(2-chloro-6-methoxyphenylacetyl)-2,3-dimethyl-2-aminovaleric acid
N-(2-chloro-6-methoxyphenylacetyl)-1-amino-cyclopentanecarboxylic acid
N-(2-chloro-6-methoxyphenylacetyl)-1-amino-cyclohexanecarboxylic acid
N-(2-chloro-6-methoxyphenylacetyl)-1-amino-cycloheptanecarboxylic acid
N-(2-chloro-6-methoxyphenylacetyl)-1-amino-cyclooctanecarboxylic acid
N-(2-chloro-4-methoxyphenylacetyl)-1-amino-2-methyl-cyclohexanecarboxylic acid
N-(2-chloro-4-methoxyphenylacetyl)-1-amino-3-methyl-cyclohexanecarboxylic acid
N-(2-chloro-4-methoxyphenylacetyl)-1-amino-4-methyl-cyclohexanecarboxylic acid
N-(2-chloro-4-methoxyphenylacetyl)-1-amino-3,4-dimethyl-cyclohexanecarboxylic acid
N-(2-chloro-4-methoxyphenylacetyl)-1-amino-4-ethyl-cyclohexanecarboxylic acid
N-(2-chloro-4-methoxyphenylacetyl)-1-amino-4-isopropyl-cyclohexanecarboxylic acid
N-(2-chloro-4-methoxyphenylacetyl)-1-amino-4-tert-butyl-cyclohexanecarboxylic acid
N-(2-chloro-4-methoxyphenylacetyl)-1-amino-4-methoxy-cyclohexanecarboxylic acid
N-(4-chloro-2-methoxyphenylacetyl)-1-amino-2-methyl-cyclohexanecarboxylic acid
N-(4-chloro-2-methoxyphenylacetyl)-1-amino-3-methyl-cyclohexanecarboxylic acid
N-(4-chloro-2-methoxyphenylacetyl)-1-amino-4-methyl-cyclohexanecarboxylic acid
N-(4-chloro-2-methoxyphenylacetyl)-1-amino-3,4-dimethyl-cyclohexanecarboxylic acid
N-(4-chloro-2-methoxyphenylacetyl)-1-amino-4-ethyl-cyclohexanecarboxylic acid
N-(4-chloro-2-methoxyphenylacetyl)-1-amino-4-isopropyl-cyclohexanecarboxylic acid
N-(4-chloro-2-methoxyphenylacetyl)-1-amino-4-tert-butyl-cyclohexanecarboxylic acid
N-(4-chloro-2-methoxyphenylacetyl)-1-amino-4-methoxy-cyclohexanecarboxylic acid
N-(2-chloro-6-methoxyphenylacetyl)-1-amino-2-methyl-cyclohexanecarboxylic acid
N-(2-chloro-6-methoxyphenylacetyl)-1-amino-3-methyl-cyclohexanecarboxylic acid
N-(2-chloro-6-methoxyphenylacetyl)-1-amino-4-methyl-cyclohexanecarboxylic acid
N-(2-chloro-6-methoxyphenylacetyl)-1-amino-3,4-dimethyl-cyclohexanecarboxylic acid
N-(2-chloro-6-methoxyphenylacetyl)-1-amino-4-ethyl-cyclohexanecarboxylic acid
N-(2-chloro-6-methoxyphenylacetyl)-1-amino-4-isopropyl-cyclohexanecarboxylic acid
N-(2-chloro-6-methoxyphenylacetyl)-1-amino-4-tert-butyl-cyclohexanecarboxylic acid
N-(2-chloro-6-methoxyphenylacetyl)-1-amino-4-methoxy-cyclohexanecarboxylic acid
Compounds of the formula (IIa) can be obtained, for example, from the phenylacetyl halides of the formula (XV) and amino acids of the formula (XIVa) by the method of Schotten-Baumann (Organikum [Laboratory Practical Organic Chemistry], 9th Edition, 446 (1970) VEB Deutscher Verlag der Wissenschaften, Berlin).
The phenylacetyl halides of the formula (XV) 
in which
X, Y and Z have the abovementioned meanings and
Hal represents bromine or chlorine are new with the exception of the compound 2-chloro-4-methoxyphenylacetyl chloride
(cf. J. Polym. Sci., Part A, Polym. Chem. 20, 997 (1992), FR-2 054 532).
The new phenylacetyl halides of the formula (XV) are obtained when phenylacetic acids of the formula (XVIII) 
in which
X, Y and Z have the abovementioned meanings, are reacted with halogenating agents, such as, for example, phosgene, phosphorus trichloride, phosphorus pentachloride, phosphorus tribromide or phosphorus pentabromide or thionyl chloride, if appropriate in the presence of an inert diluent, such as hydrocarbons or halogenated hydrocarbons, at temperatures between xe2x88x9230xc2x0 C. and 150xc2x0 C., preferably between xe2x88x9220xc2x0 C. and 100xc2x0 C.
Some of the phenylacetic acids of the formula (XVIII) are known and/or can be prepared for example by the following equation: 
X, Y and Z in formulae (XIX), (XX), (XXI) and (XVIII) have the abovementioned meanings.
The toluenes of the formula (XIX) are generally known compounds of organic chemistry.
The acid halides of the formula (III), carboxylic anhydrides of the formula (IV), chloroformic esters or chloroformic thioesters of the formula (V), chloromonothioformic esters or chlorodithioformic esters of the formula (VI), allyl halides of the formula (VII), sulfonyl chlorides of the formula (VIII), phosphorus compounds of the formula (IX) and metal hydroxides or amines of the formulae (X) and (XI) as well as isocyanates, isothiocyanates or carbamoyl chlorides of the formula (XIII), which are furthermore required as starting substances for carrying out processes (B), (C), (D), (E), (F) (G) and (H) according to the invention are generally known compounds of organic or inorganic chemistry.
Process (A) is characterized in that compound of the formula (II) in which A, B, X, Y, Z and R8 have the abovementioned meanings are subjected to an intramolecular condensation reaction in the presence of bases.
Diluents which can be employed in process (A) according to the invention are all inert organic solvents. The following can preferably be used: hydrocarbons, such as toluene and xylene, furthermore ethers, such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycol dimethyl ether, furthermore polar solvents, such as dimethyl sulfoxide, sulfolane, diethylformamide and N-methyl-pyrrolidone, and also alcohols, such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol and tert-butanol.
Bases (deprotonating agents) which can be employed when carrying out process (A) according to the invention are all customary proton acceptors. The following can preferably be used: the oxides, hydroxides and carbonates of alkali metals and alkaline earth metals, such as sodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassium carbonate and calcium carbonate, all of which can also be employed in the presence of phase transfer catalysts such as, for example, triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464 (=methyltrialkyl (C8-C10)-ammonium chloride) or TDA 1 (=tris-(methoxyethoxyethyl)-amine). Alkali metals such as sodium or potassium can furthermore be used. Moreover, alkali metal amides, alkali metal hydrides, alkaline earth metal amides and alkaline earth metal hydrides, such as sodium amide, sodium hydride and calcium hydride, and, moreover, also alkali metal alcoholates, such as sodium methylate, sodium ethylate and potassium tert-butylate, can be employed.
When carrying out process (A) according to the invention, the reaction temperatures can be varied within a substantial range. In general, the process is carried out at temperatures between 0xc2x0 C. and 250xc2x0 C., preferably between 50xc2x0 C. and 150xc2x0 C.
Process (A) is generally carried out under atmospheric pressure.
When carrying out processes (Axcex1) and (Axcex2) according to the invention, the reactants of the formulae (II) and (IIa) and the deprotonating bases are generally employed in approximately twice the equimolar amounts. However, it is also possible to use one or the other component in a larger excess (up to 3 mol).
Process (Bxcex1) is characterized in that compounds of the formula (Ia) are reacted with carboxylic halides of the formula (III).
If the acid halides are used, then diluents which can be employed in process (Bxcex1) according to the invention are all solvents which are inert to these compounds. The following can preferably be used: hydrocarbons, such as benzine, benzene, toluene, xylene and tetralin, furthermore halogenohydrocarbons, such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, moreover ketones, such as acetone and methyl isopropyl ketone, furthermore ethers, such as diethyl ether, tetrahydrofuran and dioxane, moreover carboxylic esters, such as ethyl acetate, and also strongly polar solvents, such as dimethyl sulfoxide and sulfolane. If the acid halide is sufficiently stable to hydrolysis, the reaction can also be carried out in the presence of water.
If the corresponding carboxylic halides are used, then suitable acid-binding agents in the reaction in accordance with process (Bxcex1) according to the invention are all customary acid acceptors. The following can preferably be used: tertiary amines, such as triethylamine, pyridine, diazabicyclooctane (DABCO), diazabicycloundecane (DBU), diazabicyclononene (DBN), Hxc3xcnig base and N,N-dimethyl-aniline, furthermore alkaline earth metal oxides, such as magnesium oxide and calcium oxide, moreover alkali metal carbonates and alkaline earth metal carbonates, such as sodium carbonate, potassium carbonate and calcium carbonate, and also alkali metal hydroxides, such as sodium hydroxide and potassium hydroxide.
If carboxylic acid halides are used, the reaction temperatures in process (Bxcex1) according to the invention can be varied within a substantial range. In general, the process is carried out at temperatures between xe2x88x9220xc2x0 C. and +150xc2x0 C., preferably between 0xc2x0 C. and 100xc2x0 C.
When carrying out process (Bxcex1) according to the invention, the starting substances of the formula (Ia) and the carboxylic acid halide of the formula (III) are generally used in approximately equivalent amounts. However, it is also possible to employ the carboxylic acid halide in a larger excess (up to 5 mol). Working-up is carried out by customary methods. Process (Bxcex2) is characterized in that compounds of the formula (Ia) are reacted with carboxylic anhydrides of the formula (IV).
If, in process (Bxcex2) according to the invention, carboxylic anhydrides are used as reactants of the formula (IV), then the diluents which can be used are preferably those which are also preferred when acid halides are used. Besides, an excess of a carboxylic anhydride may also simultaneously act as the diluent.
When using carboxylic anhydrides, the reaction temperatures in process (Bxcex2) according to the invention can be varied within a substantial range. In general, the process is carried out at temperatures between xe2x88x9220xc2x0 C. and +150xc2x0 C., preferably between 020  C. and 100xc2x0 C.
When carrying out the process according to the invention, the starting substances of the formula (Ia) and the carboxylic anhydride of the formula (IV) are generally used in approximately equivalent amounts. However, it is also possible to employ the carboxylic anhydride in a larger excess (up to 5 ml). Working-up is carried out by customary methods.
In general, a procedure is followed in which diluent and excess of carboxylic anhydride as well as the carboxylic acid which forms are removed by distillation or by washing with an organic solvent or water. Process (C) is characterized in that compounds of the formula (Ia) are reacted with chloroformic esters or chloroformic thioesters of the formula (V).
If the corresponding chloroformic esters or chloroformic thioesters are used, then suitable acid-binding agents in the reaction in accordance with process (C) according to the invention are all customary acid acceptors. The following can preferably be used: tertiary amines, such as triethylamine, pyridine, (DABCO), (DBU), (DBA), Hxc3xcnig base and N,N-dimethyl-aniline, furthermore alkaline earth metal oxides, such as magnesium oxide and calcium oxide, moreover alkali metal carbonates and alkaline earth metal carbonates, such as sodium carbonate, potassium carbonate and calcium carbonate, and also alkali metal hydroxides, such as sodium hydroxide and potassium hydroxide.
When using the chloroformic esters or chloroformic thioesters, then diluents which can be employed in process (C) according to the invention are all solvents which are inert to these carbons. The following can preferably be used: hydrocarbons, such as benzine, benzene, toluene, xylene and tetralin, furthermore halogenohydrocarbons, such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, moreover ketones, such as acetone and methyl isopropyl ketone, furthermore ethers, such as diethyl ether, tetrahydrofuran and dioxane, moreover carboxylic esters, such as ethyl acetate, and also strongly polar solvents, such as dimethyl sulfoxide and sulfolane.
When using the chloroformic esters or chloroformic thioesters as carboxylic acid derivatives of the formula (V), the reaction temperatures when carrying out process (C) according to the invention can be varied within a substantial range. If the process is carried out in the presence of a diluent and of an acid-binding agent, then the reaction temperatures are generally between xe2x88x9220xc2x0 C. and +100xc2x0 C., preferably between 0xc2x0 C. and 50xc2x0 C.
Process (C) according to the invention is generally carried out under atmospheric pressure.
When carrying out process (C) according to the invention, the starting substances of the formula (Ia) and the corresponding chloroformic ester or chloroformic thioester of the formula (V) are generally used in approximately equivalent amounts. however, it is also possible to employ one or the other component in a larger excess (up to 2 mol). Working-up is then carried out by customary methods. In general, a procedure is followed in which the salts which have precipitated are removed and the reaction mixture which remains is concentrated by stripping of the diluent.
In preparation process (Dxcex1), approximately 1 mol of chloromonothioformic ester or chlorodithioformic ester of the formula (VI) is reacted per mole of starting compound of the formula (Ia) at 0 to 120xc2x0 C., preferably at 20 to 60xc2x0 C.
Suitable diluents which are optionally added are all inert polar organic solvents, such as ethers, amides, sulfones, sulfoxides, but also halogenoalkanes.
Dimethyl sulfoxide, tetrahydrofuran dimethylformamide or methylene chloride are preferably employed.
If, in a preferred embodiment, the enolate salt of the compound (Ia) is synthesized by adding strong deprotonating agents, such as, for example, sodium hydride or potassium tertiary-butylate, a further addition of acid-binding agents can be dispensed with.
If acid-binding agents are employed, then customary inorganic or organic bases are suitable, and sodium hydroxide, sodium carbonate, potassium carbonate, pyridine and triethylamine may be mentioned by way of example.
The reaction can be carried out under atmospheric pressure or under elevated pressure, it is preferably carried out under atmospheric pressure. Working-up is carried out by customary methods.
In preparation process (Dxcex2), an equimolar amount or an excess of carbon disulfide is added per mole of starting compound of the formula (Ia). This process is preferably carried out at temperatures from 0 to 50xc2x0 C. and, in particular, at 20 to 30xc2x0 C.
It is frequently expedient first to prepare the corresponding salt from the compound of the formula (Ia) by adding a deprotonating agent (such as, for example, potassium tertiary-butylate or sodium hydride). The compound (Ia) is reacted with carbon disulfide until the formation of the intermediate is complete, for example after stirring for several hours at room temperature.
The product is further reacted with the alkyl halide of the formula (VII) at, preferably, 0 to 70xc2x0 C. and, in particular, 20 to 50xc2x0 C. At least an equimolar amount of alkyl halide is employed.
The process is carried out under atmospheric pressure or under elevated pressure, preferably under atmospheric pressure.
Again, working-up is carried out by customary methods.
In preparation process (E), approximately 1 mol of sulfonyl chloride (VIII) is reacted per mole of starting compound of the formula (Ia) at xe2x88x9220 to 150xc2x0 C., preferably 20 to 70xc2x0 C.
Suitable diluents which are optionally added are all inert polar organic solvents such as ethers, amides, nitriles, sulfones, sulfoxides or halogenated hydrocarbons such as methylene chloride.
Dimethyl sulfoxide, tetrahydrofuran, dimethylformamide, dimethyl sulfide or methylenechloride are preferably employed.
If, in a preferred embodiment, the enolate salt of the compound (Ia) is synthesized by adding strong deprotonating agents, such as, for example, sodium hydride or potassium tertiary-butylate, a further addition of acid-binding agents can be dispensed with.
If acid-binding agents are employed, then customary inorganic or organic bases are suitable, and sodium hydroxide, sodium carbonate, potassium carbonate, pyridine and triethylamine may be mentioned by way of example.
The reaction can be carried out under atmospheric pressure or under elevated pressure, it is preferably carried out under atmospheric pressure. Working-up is carried out by customary methods.
To obtain compounds of the structure (Ie) in preparation process (F), 1 to 2, preferably 1 to 1.3, mol of the phosphorus compound of the formula (IX) are reacted per mole of compounds of the formula (Ia) at temperatures between xe2x88x9240xc2x0 C. and 150xc2x0 C., preferably between xe2x88x9210 and 110xc2x0 C.
Suitable diluents which are optionally added are all inert polar organic solvents such as ethers, amides, nitriles, alcohols, sulfides, sulfones, sulfoxides and the like.
Acetonitrile, dimethyl sulfoxide, tetrahydrofuran, dimethylformamide or methylene chloride are preferably employed.
Suitable acid-binding agents which are optionally added are customary inorganic or organic bases, such as hydroxides, carbonates or amines. Sodium hydroxide, sodium carbonate, potassium carbonate, pyridine and triethylamine may be mentioned by way of example.
The reaction can be carried out under atmospheric pressure or under elevated pressure, it is preferably carried out under atmospheric pressure. Working-up is carried out by customary methods of organic chemistry. The end products obtained are preferably purified by crystallization, chromatography or by so-called xe2x80x9cincipient distillationxe2x80x9d, i.e. removal of the volatile components in vacuo.
Process (G) is characterized in that compounds of the formula (Ia) are reacted with metal compounds (X) or amines (XI).
Diluents which can be employed in the process according to the invention are preferably ethers, such as tetrahydrofuran, dioxane or diethyl ether, or else alcohols, such as methanol, ethanol or isopropanol, but also water. Process (G) according to the invention is generally carried out under atmospheric pressure. The reaction temperatures are generally between xe2x88x9220xc2x0 C. and 100xc2x0 C., preferably between 0xc2x0 C. and 50xc2x0 C.
In preparation process (Hxcex1), approximately 1 mol of isocyanate of the formula (XII) is reacted per mole of starting compound of the formula (Ia) at 0 to 100xc2x0 C., preferably 20 to 50xc2x0 C.
Suitable diluents which are optionally added are all inert organic solvents, such as ethers, amides, nitriles, sulfones or sulfoxides.
If appropriate, catalysts may be added to accelerate the reaction. Catalysts which can very advantageously be employed are organotin compounds such as, for example dibutyltin dilaurate. The process is preferably carried out under atmospheric pressure.
In preparation process (Hxcex2), approximately 1 mol of carbamoyl chloride of the formula (XIII) is reacted per mole of starting compounds of the formula (Ia) at 0 to 150xc2x0 C., preferably 20 to 70xc2x0 C.
Suitable diluents which are optionally added are all inert polar organic solvents, such as ethers, amides, sulfones, sulfoxides or halogenated hydrocarbons.
Dimethyl sulfoxide, tetrahydrofuran, dimethylformamide or methylene chloride are preferably employed.
If, in a preferred embodiment, the enolate salt of the compound (Ia) is synthesized by adding strong deprotonating agents (such as, for example, sodium hydride or potassium tertiary-butylate), a further addition of acid-binding agents can be dispensed with.
If acid-binding agents are employed, then suitable substances are customary inorganic or organic bases, and sodium hydroxide, sodium carbonate, potassium carbonate, triethylamine or pyridine may be mentioned by way of example.
The reaction can be carried out under atmospheric pressure or under elevated pressure, it is preferably carried out under atmospheric pressure. Working-up is carried out by customary methods.
The active compounds are suitable for combating animal pests, preferably anthropods and nematodes particularly insects and arachnids encountered in agriculture, in forests, in the protection of stored products and of materials, and in the hygiene sector. They are active against normally sensitive and resistant species and against all or some stages of development. The above-mentioned pests include:
From the order of the Isopoda, for example, Oniscus asellus, Armadillidium vulgare and Porcellio scaber. From the order of the Diplopoda, for example, Blaniulus guttulatus. From the order of the Chilopoda, for example, Geophilus carpophagus and Scutigera spec. From the order of the Symphyla, for example, Scutigerella immaculata. From the order of the Thysanura, for example, Lepisma saccharina. From the order of the Collembola, for example, Onychiurus armatus. 
From the order of the Orthoptera, for example, Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis and Schistocerca gregaria. 
From the order of the Dermaptera, for example, Forficula auricularia. From the order of the Isoptera, for example, Reticulitermes spp.
From the order of the Anoplura, for example, Phylloxera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp. and Linognathus spp.
From the order of the Mallophaga, for example, Trichodectes spp. and Damalinea spp. From the order of the Thysanoptera, for example, Hercinothrips femoralis and Thrips tabaci. 
From the order of the Heteroptera, for example. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus and Triatoma spp.
From the order of the Homoptera, for example, Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. and Psylla spp.
From the order of the Lepidoptera, for example, Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis app., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Spodoptera exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima and Tortrix viridana. 
From the order of the Coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus sp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis and Costelytra zealandica. 
From the order of the Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa spp.
From the order of the Diptera, for example, Aedes spp., Anopheles spp., Culex app., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra app., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus app., Hypoderma app., Tabanus app., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae and Tipula paludosa. 
From the order of the Siphonaptera, for example, Xenopsylla cheopis and Ceratopyllus sp. From the order of the Arachnida, for example, Scorpio maurus and Latrodectus mactans. 
From the order of the Acarina, for example, Acarus siro, Argas Op., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp. and Tetranychus pp.
The active compounds according to the invention are distinguished by powerful insecticidal and acaricidal activity.
They can be employed particularly successfully for combating plant-injurious insects, such as, for example, against the larvae of the mustard beetle (Phaedon cochleariae), against the larvae of the green rice leafhopper (Nephotettix cincticeps) or against diamond-back moth caterpillars (Plutella maculipennis).
The compounds according to the invention also show a good activity against Venturia inaequalis. 
The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with active compound, and very fine capsules in polymeric substances.
These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is, liquid solvents and/or solid carriers, optionally with the use of surface-active agents, that is, emulsifying agents and/or dispersing agents, and/or foam-forming agents.
In the case of the use of water as an extender, organic solvents can, for example, also be used as auxiliary solvents. As liquid solvents, there are suitable in the main: aromatics, such as xylene, toluene or alkyl-naphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example mineral oil fractions, mineral and vegetable oils, alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide, as well as water.
As solid carriers there are suitable: for example Bum Bats and ground natural mineral, such as kaolins, clays, talc, chalk quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as highly-disperse silica, alumina and silicates; as solid carriers for granules there are suitable: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cob and tobacco stalks; as emulsifying and/or foam-forming agents there are suitable: for example no-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates as well as a hydrolysis products; as dispersing agents there are suitable; for example lignin-sulfite waste liquors and methylcellulose.
Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations. Other additives can be mineral and vegetable oils.
It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dye-stuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
The formulations in general contain between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90%.
The active compound according to the invention can be present in its commercially available formulations and in the use forms, prepared from these formulations, as a mixture with other active compounds, such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, growth-regulating substances or herbicides. The insecticides include, for example, phosphates, carbamates, carboxylates, chlorinated hydrocarbons, phenylureas, substances produced by micooorganisms, or the like.
The following compounds may be mentioned: acrinathrin, alphmamethrin, betacyfluthrin, bifenthrin, brofenprox, cis-Reamethrin, clocythrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin, deltamethrin, esfenvalerate, ethofenprox, fenpropathrin, fenvalerate, flucythrinate, fluvalinate, lambda-cyhalothrin, permethrin, pyresmethrin, pyrethrum, silafluofen, tralomethrin, zetamethrin,
alanycarb, bendiocarb, benfuracarb, bufencarb, butocarboxim, carbaryl, cartap, ethiofencarb, fenobucarb, fenoxycarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, promecarb, propoxur, terbam, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb,
acephate, azinphos A, azinphos M, bromophos A, cadusafos, carbophenothion, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos M, cyansphos, demeton M, demeton-S-methyl, demeton S, diazinon, dichlorvos, dicliphos, dichlofenthion, dicrotophos, dimethoate, dimethylvinphos, dioxathion, disulfoton, edifenphos, ethion, etrimphos, fenitrothion, fenthion, fonophos formothion, heptenophos, iprobenfos, isazophos, isoxathion, phorate, malathion, mecarbam, mevinphos, mesulfenphos, methacrifos, methamidophos, naled, omethoate, oxydemethon M, oxydeprodrofos, parathion A, parathion M, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos A, pirimiphos M, propaphos, prothiophos, prothoate, pyraclophos, pyridaphention, quinalphos, salithion, sebufos, sulfotep, sulprofos, tetrachlorvinphos, temephos, thiomethon, thionazin, trichlorfon, triazophos, vamidothion,
buprofezin, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, pyriproxifen, tebufenozide, teflubenzuron, triflumuron,
imidacloprid, nitenpyram,
abamectin, amitraz, avermectin, azadirachtin, bensultap, Bacillus thuringiensis, cyromazine, diafenthiuron, emamectin, ethofenprox, fenpyrad, fipronil, flufenprox, lufenuron, metaldehyde, milbemectin, pymetrozine, tebufenpyrad, triazuron,
aldicarb, bendiocarb, benfuracarb, carbofuran, carbosulfan, chlorethoxyfos, cloethocarb, disulfoton, ethoprophos, etrimphos, fenamiphos, fipronil, fonofos, fosthiazate, furathiocarb, HCH, isazophos, isofenphos, methiocarb, monocrotophos, nitenpyram, oxamyl, phorate, phoxim, prothiofos, pyrachlofos, sebufos, silafluofen, tebupirimiphos, tefluthrin, terbufos, thiodicarb, thiafenox,
azocyclotin, butylpyridaben, clofentezine, cyhexatin, diafenthiuron, diethion, emamectin, fenazaquin, fenbutatin, oxide, fenothiocarb, fenpropathrin, fenpyrad, fenpyroximate, fluazinam, fluazuron, flucycloxuron, flufenoxuron, fluvalinate, fubfenprox, hexythiazox, ivermectin, methidathion, monocrotophos, moxidectin, naled, phosalone, profenofos, pyraclofos, pyridaben, pyrimidifen, tebufenpyrad, thuringiensin, triarathene,
the compound of the formula 
and the compound of the formula 
The active compound according to the invention can furthermore be present in its commercially available formulations and in the use forms, prepared from these formulations, as a mixture with synergistic agents. Synergistic agents are compounds which increase the action of the active compounds, without it being necessary for the synergistic agent added to be active itself.
The active compound content of the use forms prepared from the commercially available formulations can vary within wide ranges. The active compound concentration of the use forms can be from 0.0000001 to 95% by weight of active compound, preferably between 0.0001 and 1% by weight.
Application is effected in the customary manner adapted compound to suit the use forms.
When used against hygiene pests and stored-product pests, the active compound is distinguished by an outstanding residual action on wood and clay and by a good stability to alkali on limed surfaces.
Preparation and use of the active compound according to the invention can be seen from the examples which follow.